Stockbridge Vacation Packages 2026 from $338

Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Berkshire Mountain Lodge

$338

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

The Whitlock

$463

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

The Landing Hotel at Rivers Casino Schenectady

Nothside

$756

per person

Nov 6 - Nov 9

found 2 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Amsterdam Castle

$500

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (HOU) to Albany (ALB)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A terrace and express check-out are also provided.

Holiday Inn Club Vacations Oak 'n Spruce Resort

$371

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Top Stockbridge hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$236 total

Sep 30 - Oct 1

Total with taxes and fees

This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Spa

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

$559 nightly

$625 total

Oct 12 - Oct 13

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

Pool

Breakfast included

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$136 total

Sep 22 - Sep 23

Total with taxes and fees

This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Oct 21 - Oct 22

Total with taxes and fees

Pool

Hot Tub

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$101 nightly

$113 total

Oct 18 - Oct 19

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.

Breakfast included

Parking included

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$130 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Stockbridge

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

See properties

Frequently asked questions

How much are vacation packages to Stockbridge?

Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $338. Providing both flights and hotels, these terrific deals are a simple way to visit more of our wonderful planet.

How long should my Stockbridge vacation be?

Many visitors stay roughly 2 nights in Stockbridge. But what works for them mightn't work for you. Whether you opt to stay for a few days or a few weeks, you'll enjoy discovering all the wonderful things that this place has to offer.

Where can I get the best vacation package deals for Stockbridge?

There are awesome Stockbridge package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you're ready to cross another place off your travel bucket list.

Why should I book my Stockbridge vacation bundle with Travelocity?

Because we believe in creating unforgettable travel experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our customer support is on hand 24/7 to make sure you're never alone. We also offer a Price Match Guarantee, so you can book your trip knowing you've scored the best deal around. If you find a lower price, we'll match it!

Can I save on my Stockbridge car rental if I book it with my hotel or flight?

Combining your flight, hotel and car into a Stockbridge vacation package is the best way to score better prices. Plus, having your own wheels gives you total freedom to get to all those big sights you'd like to see. Sitting 110 mi away from Stockbridge, Times Square is one attraction that should be on your can't-miss list. Fasten your seat belt and make a day trip of it.

Which airport is best for Stockbridge?

Bradley Intl. Airport (BDL) is popular. It's situated approximately 40 mi southeast of Stockbridge. Other options worth considering are Albany Intl. Airport (ALB) (40 mi away from central Stockbridge) and Hartford, CT (HFD-Hartford - Brainard) (50 mi away from central Stockbridge).

What is there to do in Stockbridge?

There is a certain magic as you wander through the streets of Stockbridge. National Shrine of the Divine Mercy and Norman Rockwell Museum are just a couple of attractions that make this city such a sought-after destination, so put them at the top of your to-do list.

Where should I stay when visiting Stockbridge?

The The Red Lion Inn is recommended by many travelers. Book now before it's too late.